3553-80-8

Basic information

• Product Name: ethyl diethylcarbamate
• Synonyms: ethyl diethylcarbamate;Diethyl urethane;N,N-Diethylcarbamic acid ethyl ester
• CAS NO: 3553-80-8
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.1995
• EINECS: 222-607-1
• Mol File: 3553-80-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 10.63°C (estimate)
• Boiling Point: 228.04°C (estimate)
• Flash Point: 59.3°C
• Appearance: /
• Density: 0.9441 (estimate)
• Vapor Pressure: 1.2mmHg at 25°C
• Refractive Index: 1.4206 (estimate)
• CAS DataBase Reference: ethyl diethylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl diethylcarbamate(3553-80-8)
• EPA Substance Registry System: ethyl diethylcarbamate(3553-80-8)

Safety Data

• Hazardous Substances Data: 3553-80-8(Hazardous Substances Data)

Usage

General Description

Ethyl diethylcarbamate (DEC), also known as carbamates, is a chemical compound commonly used as a pesticide and insect repellent. It is a colorless, odorless liquid that is highly soluble in water and is also used as a pharmaceutical ingredient. DEC is known to have insecticidal, acaricidal, and anthelmintic properties, making it effective in controlling pests and parasites. However, prolonged exposure to DEC has been linked to negative health effects, including respiratory distress, skin irritation, and potential carcinogenic effects. Therefore, its use is regulated and restricted in certain regions to minimize its impact on human health and the environment.

InChI:InChI=1/C7H15NO2/c1-4-8(5-2)7(9)10-6-3/h4-6H2,1-3H3

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 109-89-7 diethylamine 
• 121-44-8 triethylamine 
• 71-43-2 benzene 
• 64-17-5 ethanol 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 3741-66-0 Ethyl benzoyl carbonate 
• 830-67-1 ethyl 1H-benzo[d][1,2,3]triazole-1-carboxylate 
• 52903-10-3 C₁₁H₂₅N₂O₃P 
• 124-38-9 carbon dioxide 
• 21392-71-2 1-(Diethylaminocarbonyl)aziridine 
• 101-41-7 benzeneacetic acid methyl ester 
• 78-09-1 orthocarbonic acid tetraethyl ester 
• 660-68-4 diethyl amine hydrochloride 

Downstream Products

• 1114-51-8 N,N-diethylpropanamide 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 74-85-1 ethene 
• 124-38-9 carbon dioxide 
• 109-89-7 diethylamine 
• 623-78-9 ethyl N-ethylcarbamate 
• 864364-29-4 4,4'-bis(tert-butylthio)benzophenone 
• 90021-26-4 4,4'-Bis-methoxymethyl benzophenone 
• 685-91-6 diethylacetamide 

Relevant articles and documents

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Gas-phase elimination kinetics of ethyl, isopropyl and tert-butyl N,N-diethylcarbamates. Application of Taft-Topsom correlation for substituents other than carbon at the acid side of organic ethyl esters

The elimination kinetics of ethyl, isopropyl and tert-butyl N,N-diethylcarbamates were investigated in a static reaction vessel over the temperature range 220-400°C and pressure range 17-160 Torr. These reactions are homogeneous, unimolecular and follow a first-order rate law. The temperature dependance of the rate coefficients is given by the following equations: for ethyl N,N-diethylcarbamate, log k1 (s-1) = (11.47 ± 0.25) - (178.4 ± 3.1) kJ mol-1 (2.303 RT)-1, for isopropyl N,N-diethylcarbamate, log k1 (s-1) = (12.83 ± 0.70) - (179.8 ± 7.9) kJ mol-1 (2.303 RT)-1; and for tert-butyl N,N-diethylcarbamate, log k1 (s-1) = (12.87 ± 0.62) - (158.6 ± 6.2) kJ mol-1 (2.303 RT)-1. The branching of the alkyl groups at the alcohol side of the ester exerts a significant effect on the rates in the order tert-butyl > isopropyl > ethyl. In addition, the presence of different substituents other than carbon at the acid side of organic ethyl esters gives the best correlation when using the Taft-Topsom equation: log k/kH = -(0.68 ± 0.12)σs + (2.57 ± 0.12)σF - (1.18 ± 0.27)σR (r = 0.984 ± 0.119 at 400°C). According to this relationship, the field (inductive) effect of the substituent has the greatest influence on rate enhancement, while the polarizability (steric) and resonance factors, although small in effect, favour the elimination process. Copyright

REACTIVITY OF COORDINATED LIGANDS. METAL-ASSISTED ELECTROPHILIC REACTIONS AT THE O-COORDINATED CARBON DIOXIDE FRAGMENT OF THE N,N-DIALKYLCARBAMATO GROUP: FORMATION AND DECOMPOSITION OF MIXED N,N-DIALKYLCARBAMIC ANHYDRIDES, R2NC(O)O-E

N,N-Dialkylcarbamato complexes, , of sodium, copper(II), manganese(II), cobalt(II), titanium(III), vanadium(III) and iron(III) react with electrophilic reagents under mild conditions giving the products arising from the attack at the oxygen atom of the metal-coordinated carbamato group. Thus, for example, acyl halides R'COCl give the mixed carbamic-carboxylic anhydrides R2N-C(O)O-C(O)R', independent of the nature of the metal, either as an unstable intermediate or as a kinetically-controlled product (R = i-Pr, R' = Me, Ph). Vanadium(III), titanium(III) and iron(III) dialkylcarbamato complexes react incompletely with R'COCl, giving chloro-dialkylcarbamato metal complexes. The manganese(II) diethylcarbamato derivative reacts with ClCOOEt, COCl2, ClSOOEt, SOCl2 or ClP(OEt)2; in these cases, experimental evidence exists that the organic halides react in a way similar to R'COCl, i.e. via O-functionalization of the manganese-coordinated diethylcarbamato group and formation of an Et2NC(O)OE-type compound with E=COOEt, COCl, SOOEt, SOCl, P(OEt)2. The mechanism of Et2NC(O)OE decomposition has been investigated by examining the reaction of the 13C-labelled Mn6(O2CNEt2)12 with MeCOCl, COCl2, ClCOOEt or ClSOOEt. The IR spectroscopic and GC-mass analysis of the reaction mixtures showed loss of 13CO2, while the organic product was unlabelled. This can only be consistent with the cleavage of the RN-13C bond within the intermediate anhydride. A classification of metal-assisted reactions is presented in the Appendix.